Will Shortz + Grief
The secret weapon in my grief journey
My relationship with crosswords is hinged on snobbery. My snobbery.
I grew up in South Dakota thinking that the New York Times was actually the paper of record, not just the paper that thought they were the paper of record.1 During college I would multi-task during lectures, sliding the daily NYT crossword back and forth with my seatmates. Back then, I maxed out skill-wise at the Wednesday or Thursday puzzle2. The Saturday puzzle was a mirage, visible but unattainable. I lived in Brooklyn and felt the bliss of buying the paper copy of the NYT while carrying a bagged toasted sesame bagel on my way to work. What a way for a City Girl to start the day.
As I grew older, I got better at the NYT crossword, to the point where the Friday puzzle, while still a beast, was in the neighborhood of my wheelhouse. If I collaborated with someone, I could even feel ok about the Saturday puzzle. The best collaborator I had — by far — was my mom. She had a clever head for word games of all kinds, but the depth of her education and the breadth of her bookshelf made her a savant at crosswords. The early days of the week took her mere minutes. Even Friday and Saturday, she would methodically zip it up in under a couple hours.
How fortunate was I that my next hometown (St. Paul) had the daily NYT crossword in its printed paper. I could live outside of New York and still keep up with my mom on the daily puzzle. We exchanged the occasional text about a hard or punny clue. I asked for help sometimes; she didn’t need help. The Star-Tribune also had the LA Times puzzle on the same page. I never, not once, even considered doing that puzzle; my mom and I knew the LA Times puzzle was too easy. Embarrassingly easy, really. See? Snob.
As my mom got older and slowed down, and as a cancer diagnosis curtailed so much of what brought joy to her days, the crossword puzzle remained. Lunchtime (cheese and crackers) saw her hunched over the puzzle, then a shift to her favorite comfy chair with an icy glass of Diet Caffeine Free Pepsi (we failed her here) and the puzzle page folded over on a book for a good writing surface. She was particular about her puzzling pens (NEVER A PENCIL). Elegant letters, almost cursive looking, and so distinctive. I can’t think of one time that she DNF’ed a puzzle.
Change comes fast and delivers multiple blows. The Star-Tribune stopped delivering to South Dakota so my mom’s access to the paper puzzle ended. I switched to a digital paper subscription (the puzzle was my last reason to get the paper copy) and can’t find a simple way to get a paper version of the daily NYT puzzle. I don’t like doing puzzles on my phone — just more staring at screens and nowhere near as satisfying for me.3
Most importantly, my mom died. And puzzling now seems fraught with unattended-to grief. I’m scared of them and scared of what I might feel. Last week I was on a flight, and I found an old NYT Sunday puzzle book that belonged to my mom in my bag, a bag I hadn’t used since before my mom died. I pulled it out and saw that she had started but not finished one of the puzzles (surely for time reasons and not skill!)
I cried on the plane. I felt urgently that I needed to complete this for her. I realized that some of the clues, as well as the title, were ludicrous and mourned that we couldn’t laugh about them. Herewith in my mom’s gorgeous hand:
NB:
102 across Take a Big Whisk. Please someone use this as a story title.
40 across The Life of Wiley feels like it should have big meaning to me but I can’t decide what it is yet.
I finished her puzzle on the plane, with the stranger next to me side-eyeing my tears.
The last box I filled was 65 across. Answer: clam. Mom would’ve loved that old-timey answer.
I hope I scratched an itch for my mom, clearing out an undone task. People always say to keep talking to the ones who’ve left, and crosswords might be my way of talking to her in the years to come. I wonder if Will Shortz knows that his work is becoming a seance of sorts. I’d like to think he’d smile at that.
Substack is a place for me to yap about all things obituary but also all things life. One of the greatest joys of building this crazy social media presence has been the opportunity to speak to groups of all sizes in a variety of venues about the essential life advice that comes from obituaries. Anybody — in work settings, at home, in relationships — can benefit from hearing the stories of the dead and how they can impact our own choices. It’s the best chapter of my life so far. If you’re interested in learning more about me as a speaker, get in touch: tipsfromdeadpeople@gmail.com.
Not at all the topic of this post, but the both-sides-ing and fearful temporizing of the political commentary of the last ten years made me finally break up with the Times. I grieve that all the time and hope we can reunite under better circumstances! I’ll be here!
If you know you know, but if you don’t, the NYT daily puzzle starts with the easiest on Monday. Maximum difficulty on Saturday. Most fun on Sunday, which has a theme, but is about the difficulty level of a Weds or Thursday aside from cracking the theme.
Who can help a girl figure out how to get a simple printed copy of the daily puzzle without an expensive subscription!




My mom was also a fierce crossword puzzler (in pen)! I think this made it especially hard when she got dementia and could no longer do them. It was such a huge part of her identity and she said she did them “to keep her mind sharp”. (Sniff!)
I also recently broke up with the Times. My spouse thinks I’m crazy, but there were just too many pieces that were lazy, everyone’s-opinion-is-valid (even when it’s horrific). I feel seen! Thank you :)
Thank you, as a word puzzle girl and a girl that lost her mom too, I love this so much.